1,3-Dipolar Cycloaddition of Nitrones to Gold(III)-Bound Isocyanides
Tatyana B Anisimova
1
,
M. A. Kinzhalov
2
,
Maxim Kuznetsov
1
,
A. A. Zolotarev
2
,
Konstantin Luzyanin
2, 3
Publication type: Journal Article
Publication date: 2016-10-12
scimago Q2
wos Q1
SJR: 0.676
CiteScore: 5.1
Impact factor: 2.9
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
Treatment of gold(III)-isocyanides [AuCl3(CNR1)] (R1 = Xyl 1, Cy 2, But 3) with an equimolar amount of 5,5-dimethyl-1-pyrroline-N-oxide (4) in CH2Cl2 at −74 °C leads to the generation of the heterocyclic aminocarbene species [AuCl3{C(ONaCMe2CH2CH2CbH)═NeR1}(Na–Cb)(Cb–Ne)] 8 (for R1 = But) or gold(III) complexes cis-[AuCl2{Na(CMe2CH2CH2CbNeR1)Cd═O}(Na═Cb)(Ne–Cd)] 9 and 10 (for R1 = Xyl and Cy) in good isolated yields (75–87%). DFT calculations show that deprotonation of the endocyclic CH group in the carbene ligand leads to spontaneous N–O bond cleavage, and acidity of this group is a factor controlling the different chemical behavior of 1–3 depending on the nature of substituent R1. The reaction of equimolar amounts of the aldonitrone p-TolCH═N+(Me)O– (5) or the ketonitrones Ph2C═N+(R2)O– (R2 = Ph 6, CH2Ph 7) with 1–3 in CD2Cl2 at −70 °C in air (or under N2) revealed the formation of the carbene complexes [AuCl3{C(ONMeCaH-p-Tol)═NbR1}(Ca–Nb)] (R1 = Cy 11, Xyl 12, But 13), [AuCl3{C(ONPhCaPh2)═NbR1}(Ca–Nb)]...
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Total citations:
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Citations from 2024:
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Anisimova T. B. et al. 1,3-Dipolar Cycloaddition of Nitrones to Gold(III)-Bound Isocyanides // Organometallics. 2016. Vol. 35. No. 20. pp. 3569-3576.
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Anisimova T. B., Kinzhalov M. A., Kuznetsov M., Salgueiro da Silva M. A., Zolotarev A. A., Kukushkin V. Y., Pombeiro A. J. L., Luzyanin K. 1,3-Dipolar Cycloaddition of Nitrones to Gold(III)-Bound Isocyanides // Organometallics. 2016. Vol. 35. No. 20. pp. 3569-3576.
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TY - JOUR
DO - 10.1021/acs.organomet.6b00635
UR - https://doi.org/10.1021/acs.organomet.6b00635
TI - 1,3-Dipolar Cycloaddition of Nitrones to Gold(III)-Bound Isocyanides
T2 - Organometallics
AU - Anisimova, Tatyana B
AU - Kinzhalov, M. A.
AU - Kuznetsov, Maxim
AU - Salgueiro da Silva, M. A.
AU - Zolotarev, A. A.
AU - Kukushkin, Vadim Yu.
AU - Pombeiro, Armando J. L.
AU - Luzyanin, Konstantin
PY - 2016
DA - 2016/10/12
PB - American Chemical Society (ACS)
SP - 3569-3576
IS - 20
VL - 35
SN - 0276-7333
SN - 1520-6041
ER -
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BibTex (up to 50 authors)
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@article{2016_Anisimova,
author = {Tatyana B Anisimova and M. A. Kinzhalov and Maxim Kuznetsov and M. A. Salgueiro da Silva and A. A. Zolotarev and Vadim Yu. Kukushkin and Armando J. L. Pombeiro and Konstantin Luzyanin},
title = {1,3-Dipolar Cycloaddition of Nitrones to Gold(III)-Bound Isocyanides},
journal = {Organometallics},
year = {2016},
volume = {35},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.organomet.6b00635},
number = {20},
pages = {3569--3576},
doi = {10.1021/acs.organomet.6b00635}
}
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Anisimova, Tatyana B., et al. “1,3-Dipolar Cycloaddition of Nitrones to Gold(III)-Bound Isocyanides.” Organometallics, vol. 35, no. 20, Oct. 2016, pp. 3569-3576. https://doi.org/10.1021/acs.organomet.6b00635.
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